For months, Alan Friedman avoided the reality of a changing real estate marketplace. Content with the status quo, Friedman balked at the suggestions of his Realtor, who nudged him to refashion the Lakeview property he was attempting to rent.

Owner of a Victorian three-flat for three decades, Friedman never encountered much trouble finding a tenant. One would leave, another would enter. He never once advertised.

When tenants moved out in August 2007, however, Friedman found himself in an unfamiliar spot: a new occupant wasn't in line. For the first time in his landlord career, prospective tenants toured his apartment never to return. The apartment lingered vacant for one month, then two, and then rolled into 2008 uninhabited.

"When we didn't get action in the fall, [my Realtor] began hammering on me that I needed to make some changes," Friedman said.

Initially, he resisted. Over the course of 30 years, Friedman had made subtle changes to the century-old building. Wholesale changes, however, were not his forte.

"I had always reasoned that the apartment was filled, so there was no reason to do anything drastic. Clearly, the market had changed, my competition had shifted, and my unit paled in comparison," Friedman said.

With the apartment vacant for over 10 months, Friedman finally heeded his Realtor's advice. He painted every room in the apartment, brought in new stainless steel appliances and replaced linoleum flooring with tile. His total investment was equivalent to less than three months rent.

"Lo and behold," Friedman said, "a week after I finished the work, the apartment was rented. I needed to set it apart from the inventory on the market. I needed to modernize it enough to minimize its negatives."

Though Friedman's story concerns the rental marketplace, his tale offers a cautionary, insightful look into the present-day real estate world, one that must impress upon first glance. The home resale game has long been the toughest bout in town, but if landlords are feeling the crunch, then home sellers -- requesting a six-figure investment from buyers -- best be mindful of a new marketplace with weighty demands, those far heftier than what Friedman encountered.

"People often don't pay attention in their own home and get used to the scenario. But you get one shot to show your property, and it has to deliver off the bat," said Genie Birch, a Realtor with Koenig & Strey in the Gold Coast and a director with the Chicago Association of Realtors.

For many trying to sell a home, the thought of investing money into a property they will soon leave is a less than appealing option. In today's market, however, such a move has emerged a necessity in the majority of cases. The National Association of Realtors' (NAR) 2007 survey of American home sellers found that 55 percent remodeled or made improvements within three months of hitting the market, most investing in the neighborhood of $3,000 to make the home look fresh, modern and clean.

To be certain, sellers have increasingly taken note that a challenging marketplace demands strong action. With that knowledge, sellers remain wondering what projects must be done to boost their home's appeal. Birch suggests sellers begin with a camera.

"Often homeowners don't see problems with their homes because they know where everything is, but they're never really looking at the property," she said. "Taking photographs of the property is the best way to shift the sellers' paradigm -- they then see the scrapes on the wall, the outdated bathroom. It's often an awakening experience."

Sellers must then consider the necessary changes. For some, though surely fewer than before, decluttering and cleaning might provide the antidote. For others, particularly in neighborhoods hosting a healthy inventory as well as those homes in need of updating to reach the level of their local competition, wise money might be put into more comprehensive projects.

"Bringing a home that is substandard up to neighborhood norm generally provides a good return [on one's investment]," said NAR spokesman Walter Molony. "Historically, the biggest bang for the buck is simply taking care of cosmetics -- painting, cleaning out clutter, trimming the landscape. Of course, correcting any significant deficiency is necessary, especially in an environment where buyers have so many choices."

While kitchens and baths have traditionally delivered the most substantial returns on one's investment, industry insiders have noticed a shift as the real estate market has softened in recent years: curb appeal is now king.

"There's been a shift toward exterior replacement projects bringing the biggest remodeling returns," said Molony. "[The shift] may indicate that with more options for buyers to choose from in much of the country, curb appeal and making a good first impression is even more important. How a home presents itself from the outside suggests how it's been maintained on the inside."

In the NAR's 2007 "Cost vs. Value Report," an annual partnership with Remodeling Magazine that analyzes the value of various remodeling projects at the time of resale, three of the top four remodeling projects in the Chicago area were exterior improvements. Siding replacement delivered a near dollar-for-dollar return on one's investment while a wood deck addition and wood window replacement secured approximately 94 percent of one's initial investment.

"This year's report shows that many buyers judge a house by its exterior," Molony said.

While Birch can understand a seller's reluctance to invest additional dollars in a property they will eventually leave, she urges sellers to recognize the buyer's point of view. Simply saying that the lack of one amenity or the cost of bringing an outdated home into the 21st century is factored into the price does little to appease buyers, many of whom want to see the changes in front of their eyes.

"The buyers are looking at a home in need of repair and updating and their eyes are going cha-ching like a cash register," Birch said. "They're wondering, 'How much will this cost me?'

"Today's market is different," she continued. "The improvements a seller makes might not translate as much into monetary value as they do market time. People are going to jump on that updated, more orderly home much faster. That's just where we're at right now."

Looking back, Friedman shares disappointment that he didn't make the changes to his Lakeview apartment sooner. Though modest in both cost and commitment, the changes nevertheless secured a tenant in quick time.

"When you do the repairs, you give less negative to focus on and you're overcoming some of the objections [the tenants] can have," he said. "What I had been doing hadn't been working. I needed to make the investment. I needed to take the time. The fact of the matter is that the market had shifted and I needed to respond to that change."

Daniel P. Smith is a local freelance writer.